Welcome to Cuba! Once everyone has arrived in Havana, you’ll head deeper into the city for your first taste of Cuban adventure.

Your tour begins with a visit to a local paladar, a privately-owned restaurant where you can dive into Cuban culture through its Caribbean-influenced cuisine. After savoring the local flavors, you’ll set off on a walking tour of the city. The highlight of the afternoon is Habana Vieja, or Old Havana—a vibrant area where Cuba’s rich history and evolving future come to life in every colonial plaza and bustling street. Unlike many other colonial city centers on the island, Habana Vieja feels lively and attuned to the present rather than stuck in the past. Its rich history and colorful daily life make the vibrancy palpable.

After a full afternoon exploring Habana Vieja’s many sights, you’ll sit down to dinner at another local paladar. Later, you can either return to your casa particular (private home) for a restful night or stay out a bit longer to experience Havana’s music scene.

Have an early breakfast at your hotel and then transfer to San Antonio de Los Baños, home to the Museo del Humor, partly founded by Colombian author Gabriel García Márquez. Your cycling adventure begins with a ride through the rural Artemisa Province, an agricultural region. On your way to Las Terrazas, pass through the towns of Vereda, Caimito, Guayabal, and Cayajabos. Pause for a People-to-People experience with a local manager to learn about the role of cooperatives in the Cuban market and sample their fruit. 
 
Reach the UNESCO biosphere reserve of Las Terrazas, habitat for more than 117 bird species including the endemic tocororo and zorzal. Walk along its trails and perhaps visit a local artisan workshop. Overnight and enjoy dinner at the iconic Hotel Moka, unique for its 100-year-old tree in the lobby.
 
Biking Distance: 30.9 miles
Elevation: 1233 /  939 feet

Today, cycle along rough roads, rolling hills, and smooth paths through some of Cuba's lushest landscapes. Enjoy a fun ride with new adventures at every turn! Set off early, pedaling through La Sierra del Rosario Biosphere Reserve, where forests, grasslands, rounded hills, and waving royal palm trees surround you. Keep an eye out for incredible rock formations jutting from the earth. Follow a meandering path to Bahia Honda for a lunch stop, then pass through charming towns like Cabanas, Palma Rubia, and La Palma on the way to Vinales.

Pause in La Palma, where you'll be picked up and transferred to Vinales, a region embraced by the misty, pine-covered hills of the Sierra de los Órganos. Valley de Viñales boasts a fantastical landscape with stocky limestone mogotes rising from flat plains and labyrinths of hidden caves in rocky overhangs. Explore nearby paths, take in the immersive scenery, and unwind with dinner and a drink before bed.

Biking Distance: 38.4 Miles
Elevation gain/loss: 1953 /  2400 feet
 

Start your day with a hearty breakfast before climbing back onto your bike to explore more of the sprawling karst landscape. Pedal through plantations of bright green tobacco leaves and freshly turned, rust-colored earth, passing rural villages with porches adorned in sillo. It’s a peaceful morning ride through one of Cuba’s most serene corners.

Around lunchtime, arrive in Puerto Esperanza, a fishing village that serves as a primary port for Viñales. Expansive mango trees, said to date back to the 1800s, line the entry road, and the gentle crash of waves greets your entry into this quiet town, largely untouched by the last 50 years. Enjoy a seafront lunch here before being picked up for a transfer back to your lodgings in Viñales.

Once back in the valley with the afternoon ahead, you can walk along the informal “trail systems” winding throughout the valley or visit a nearby organic farm. These trails may lead you to the towering, vertical walls of mogotes, the pock-marked faces of caverns, or hidden river systems—all captivating sights that make this landscape unique. A farm visit allows you to connect with local people who tend the land that sustains them, providing insight into their daily lives.

Later, enjoy another dinner of fresh, authentic Cuban ingredients before settling in for the evening.

Biking Distance: 20.9 Miles
Elevation gain/loss: 853 / 1295 feet

Today, you'll have two route options for the ride, determined by current road conditions. Option B was unavailable in 2022-2023 due to bridge construction along the route, though it may open up in the future.

Option A: Ride from Viñales to the west, passing through Pons and then southeast to Pinar del Río. This challenging day takes you through mountain terrain, with around 2,000 feet of ascent and 3,000 feet of descent.

Option B: Begin your day in the lush landscapes of Viñales before transferring to Puente de Cabezas, a rural town surrounded by rolling green fields. Your ride today leads you through the San Carlos Valley, offering breathtaking views of limestone bluffs cloaked in foliage, isolated huts, and tobacco fields in rich rust hues. As the road unwinds before you, immerse yourself in the pastoral beauty, cycling along with stops for exploration and a boxed lunch. Enjoy a gentle downhill route through the scenic river valley, with friendly farmers waving as you pass. The ride concludes in the small town of Isabel Rubio, where you’ll board a bus. On the drive to Pinar del Río, pass through Cuba’s tobacco heartland, San Juan y Martínez, known for its premium tobacco leaves.

By late afternoon, arrive in Pinar del Río, a city true to its name with pine-lined riverbanks and vibrant neoclassical architecture. Settle into your accommodation, then meet up for dinner at a local restaurant.

Biking Distance: 43 Miles
Elevation gain/loss: 1467 / 1760 feet
 

Continue your travels through rural Cuba as your cycle today take you along the La Carretera Central highway passing through Herradura, Capilla, and Paseo Real de San Diego until you arrive in Fierro. Enjoy a picnic at a scenic spot en route and have the opportunity for a People-to-People interaction with local beekeepers.  Other surprises await as you discover and learn from local Cubans you meet along the way.

After your ride, board your bus and head into Havana for the night.  After getting settled into your hotel, dine of one of the city’s fine paladars and for those who wish, there’s plenty of music to explore later in the evening.

Biking Distance: 31.8 miles
Elevation gain/loss: 1175/ 1122 feet
 

Today is a day on foot as you explore Havana. In the morning, drive a short distance west to Jaimanitas, where you’ll find the fantasy world of artist José Rodríguez Fuster. Fuster transformed the once-average town into an open-air art exhibition that Picasso would have felt at home in. Walk through Fusterlandia and witness the incredible world where roofs, doorways, benches, and city blocks become expressions of the artist and iconic Cuban images.

Drive east back through Miramar, passing leafy suburbs where embassies line the streets and upscale Havana thrives. Your next stop is the Museo de Ernesto Hemingway, located in his former home at Finca Vigía. With a local guide, tour the restored facilities to gain insight into the life and mind of Cuba’s favorite literary expatriate. Afterwards, visit the seaside hamlet of Cojimar, where Hemingway kept his boat, Pilar, and find a couple of excellent paladars for lunch.

In the afternoon, take time to explore more of old Havana on foot. Walk along the Malecón, amble through the narrow streets of Habana Vieja, and, if you wish, visit one of several excellent museums in the city. It’s an immersive day of architecture, history, and the ever-evolving Cuban culture as you follow the labyrinthine paths of Havana’s history.

Late in the day, begin your final night out on the town. Explore the city as night falls, as Cubans do—in classic cars that haven’t lost their 1950s glamour—before heading to a paladar for dinner. Enjoy Havana’s salsa-filled nightlife before returning to your casa to rest up for tomorrow’s flight!

Optional ride: 10-15 miles on mostly level terrain.

 

Have an early breakfast before transferring to Jose Marti International Airport for your flight home.